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First-generation (FG) college students have been a popular subpopulation to study within educational literature as these students experience many unique challenges in their academic careers compared to their peers. Much of this research has focused on the shortcomings and obstacles these unique students face in striving for a four-year college degree, but less focus has been on the unique underlying motivational challenges. This study used a longitudinal design to follow up on a pilot study that looked at FG college students’ experience of task values regarding their engagement with transformative experience (TE). Participants were 193 undergraduate students who completed surveys on task values, more specifically their intrinsic, attainment, utility, and cost values, and their engagement in TE at three different time points across the semester. Students’ exam scores were also reported as a measurement of academic achievement. My analyses showed that FG college students reported higher levels of cost value and growth in cost value across the semester compared to non-first-generation (NFG) college students. Analyses also indicated that FG college students had significantly lower exam scores compared to NFG college students. Both FG and non-NFG college students engaged in TE at similar levels across the semester. Results of this study indicate FG college students experience academic challenges that may be related to their valuing of their educative experience, which TE may be able to help reframe their valuing of their experience. Implications for further teaching practices and interventions are discussed.